A good method of knowing when you have out of date packages is to use the utility lintpkgsrc, which can be [[Installing a package with pkgsrc]] installed from pkgtools/lintpkgsrc. Once it is installed use it to check installed packages for newer available versions:
lintpkgsrc -i
Scan Makefiles: ................
Version mismatch: 'dummy' 5.1 vs 5.2
Version mismatch: 'other_package' 2.5a vs 2.5b
The results are simple: outdated-package-name currently-installed-version -vs- currently-supported-version
See also
[[pkg_chk]]